Sukbok Chang received his B.S degree from Korea University in 1985, and M.S degree from KAIST in 1987. Then, he joined Eric N. Jacobsen's group and received his PhD in 1996 at Harvard University. He subsequently worked with Robert H. Grubbs at Caltech as a postdoctoral fellow from 1996 to 1998. In early 1998, he joined the faculty of Ewha Womans University as an assistant professor, and moved to KAIST as a full professor in 2002. In 2012, he was selected as a director of the Center for Catalytic Hydrocarbon Functionalizations at the Institute for Basic Science, which is the biggest Korean government funded research institute. He also has been working as an associate editor of the journal ACS Catalysis since 2015. In 2023, he was selected to co-run the KAIST Cross Generation Creation Lab, a laboratory designed to continue the know-how of professors about to retire through collaboration with younger professors.[3][4][5]
Major contributions
Chang's group studies new organic reactions and mechanisms with transition metal catalysis.[6] In particular, his group contributed to the development of "copper catalyzed multicomponent coupling" in the 2000s. Since 2008, his group has focused on C-H functionalization and made a number of contributions.[7]
Copper-catalyzed multicomponent coupling
Cu-catalyzed multicomponent coupling is a notable process developed by Chang's group. In 2005, they published a highly efficient and mild catalytic three component coupling between an alkyne, sulfonyl azide, and amine.[8] Unlike click chemistry which generates 1,4-triazoles as products, in this case a Cu(I) catalyst, sulfonyl azide and alkyne generate ketenimine intermediate after releasing N2 gas. This electrophilic ketenimine intermediate reacts with amines and to generate asymmetric imines as products. Chang's group also showed water,[9] alcohols,[10] the C3 position of pyrrole[11] and other nucleophiles can be used in this reaction.
Rhodium, Iridium-catalyzed C-N bond formation
Rhodium or iridium catalyzed C-H amidation and amination are other achievements of his group. In 2012, his group published rhodium catalyzed intermolecular amidation of arenes using sulfonyl azide as a nitrene precursor.[12] This reaction generates N2 as the single byproduct, doesn't need external oxidant, has broad substrate scope and high functional group tolerance. Chang's group advanced their work by using different directing groups,[13] different azides[14] and various substrates.[15] They also published that iridium also works well for C-H amidation/amination.[16][17][18]
In 2016, Chang's group discovered new nitrogen sources.[19] Their new nitrene precursor, 1,4,2-dioxazol-5-one, is more convenient to prepare, store and use compared to azides. Moreover, it has a strong affinity to the rhodium or Iridium metal center, and thus gives excellent amidation efficiency.[20] They later published selective formation of gamma-lactams via C-H amidation[21][22] with this type of nucleophile.
^Bae, Imhyuck; Han, Hoon; Chang, Sukbok (February 2005). "Highly Efficient One-Pot Synthesis ofN-Sulfonylamidines by Cu-Catalyzed Three-Component Coupling of Sulfonyl Azide, Alkyne, and Amine". Journal of the American Chemical Society. 127 (7): 2038–2039. doi:10.1021/ja0432968. ISSN0002-7863. PMID15713069.
^Cho, Seung Hwan; Yoo, Eun Jeong; Bae, Imhyuck; Chang, Sukbok (November 2005). "Copper-Catalyzed Hydrative Amide Synthesis with Terminal Alkyne, Sulfonyl Azide, and Water". Journal of the American Chemical Society. 127 (46): 16046–16047. doi:10.1021/ja056399e. ISSN0002-7863. PMID16287290.
^Yoo, Eun Jeong; Ahlquist, Mårten; Bae, Imhyuck; Sharpless, K. Barry; Fokin, Valery V.; Chang, Sukbok (July 2008). "Mechanistic Studies on the Cu-Catalyzed Three-Component Reactions of Sulfonyl Azides, 1-Alkynes and Amines, Alcohols, or Water: Dichotomy via a Common Pathway". The Journal of Organic Chemistry. 73 (14): 5520–5528. doi:10.1021/jo800733p. ISSN0022-3263. PMID18557650.
^Cho, Seung Hwan; Chang, Sukbok (2008-03-31). "Room Temperature Copper-Catalyzed 2-Functionalization of Pyrrole Rings by a Three-Component Coupling Reaction". Angewandte Chemie International Edition. 47 (15): 2836–2839. doi:10.1002/anie.200705940. ISSN1433-7851. PMID18318034.
^Kim, Ji Young; Park, Sae Hume; Ryu, Jaeyune; Cho, Seung Hwan; Kim, Seok Hwan; Chang, Sukbok (2012-05-24). "Rhodium-Catalyzed Intermolecular Amidation of Arenes with Sulfonyl Azides via Chelation-Assisted C–H Bond Activation". Journal of the American Chemical Society. 134 (22): 9110–9113. doi:10.1021/ja303527m. ISSN0002-7863. PMID22624801.
^Kim, Jinwoo; Chang, Sukbok (2014-01-27). "Iridium-Catalyzed Direct CH Amidation with Weakly Coordinating Carbonyl Directing Groups under Mild Conditions". Angewandte Chemie International Edition. 53 (8): 2203–2207. doi:10.1002/anie.201310544. ISSN1433-7851. PMID24470125.
^Kang, Taek; Kim, Youngchan; Lee, Donggun; Wang, Zhen; Chang, Sukbok (2014-03-05). "Iridium-Catalyzed Intermolecular Amidation of sp3 C–H Bonds: Late-Stage Functionalization of an Unactivated Methyl Group". Journal of the American Chemical Society. 136 (11): 4141–4144. doi:10.1021/ja501014b. ISSN0002-7863. PMID24580093.
^Park, Yoonsu; Park, Kyung Tae; Kim, Jeung Gon; Chang, Sukbok (2015-03-30). "Mechanistic Studies on the Rh(III)-Mediated Amido Transfer Process Leading to Robust C–H Amination with a New Type of Amidating Reagent". Journal of the American Chemical Society. 137 (13): 4534–4542. doi:10.1021/jacs.5b01324. ISSN0002-7863. PMID25789561.
^Park, Yoonsu; Heo, Joon; Baik, Mu-Hyun; Chang, Sukbok (2016-10-13). "Why is the Ir(III)-Mediated Amido Transfer Much Faster Than the Rh(III)-Mediated Reaction? A Combined Experimental and Computational Study". Journal of the American Chemical Society. 138 (42): 14020–14029. doi:10.1021/jacs.6b08211. ISSN0002-7863. PMID27690406.
